Desktop System Software Engineer II Chicago

Chicago;
New York, New York, United States

Alpha Sense is looking for a Desktop System Software Engineer II to join the Corporate Technology team. This is not a traditional IT support role — it sits at the intersection of enterprise endpoint engineering and desktop application diagnostics. You will own the health, behavior, and configuration of macOS and Windows endpoints at a systems level, while also serving as a technical bridge between Corporate IT and the Alpha Sense product engineering organization — with a specific focus on the behavior of Alpha Sense’s desktop applications on managed devices.

You’ll work alongside a team that manages MDM at scale using Kandji/Iru and Microsoft Intune, enforces Zero Trust security via Crowd Strike and Cloudflare, and operates in a high-velocity SaaS product environment. A core part of this role is the ability to reproduce, isolate, and help resolve issues that users encounter within Alpha Sense’s own desktop applications — requiring both deep desktop OS knowledge and genuine curiosity about how software behaves at the client layer.

You’re someone who gets energized by hard, ambiguous problems — whether that’s a desktop app that crashes only on one macOS version, an MDM policy that breaks an auto-updater, or a Crowd Strike sensor policy that silently blocks a feature. You care about the quality and reliability of the experience Alpha Sense employees have with the company’s own products every day, and you take ownership of outcomes rather than waiting for someone else to define the path forward.

You’re equally comfortable reading a system crash log and writing a precise bug report for a product engineer.

• Collaborate and contribute on the strategy and execution of macOS and Windows endpoint configuration, policy enforcement, and lifecycle management via Kandji/Iru and/or Microsoft Intune
• Build, maintain, and iterate on device enrollment workflows, configuration profiles, compliance policies, and custom scripts
• Design and enforce software deployment, patch management, and application allow listing/block listing strategies
• Collaborate with Security on EDR (Crowd Strike Falcon), Zero Trust (Cloudflare WARP/Gateway), and identity (Okta) integrations at the endpoint layer
• Maintain scripting libraries (Bash, Python, Power Shell) to automate endpoint management tasks and reduce manual intervention

• Serve as a primary technical escalation point for issues users experience within Alpha Sense’s desktop applications on managed endpoints
• Reproduce client-side issues across macOS and Windows versions, app build versions, and endpoint configurations to isolate root causes
• Investigate and diagnose desktop application behavior including crash analysis, rendering issues, performance degradation, update/upgrade failures, and OS-level permission or sandboxing conflicts
• Partner with product engineering teams to log detailed bug reports, provide environmental context, and validate fixes as they are released
• Capture crash logs, console output, network traces, and system-level diagnostics to accelerate resolution of complex application-layer problems
• Maintain a diagnostic runbook library covering common desktop application issues on Kandji/Iru- and Intune-managed devices
• Test new desktop application releases against the managed device baseline before broad rollout, flagging regressions early

• Monitor endpoint fleet health, identify systemic issues, and drive proactive remediation before issues impact users
• Contribute to internal tooling and automation to improve IT operations and reduce ticket volume
• Document configurations, processes, and runbooks in the team's knowledge base
• Participate in incident response for endpoint-related security events alongside the Security team

• 3–5 years of experience in a systems engineering, endpoint engineering, or desktop platform role (not generalist IT support)
• Deep hands‑on experience with macOS (preferably) and/or Windows at a configuration and troubleshooting level…